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yo - so my workmate is buying a house, so is moving from renting to owning.
his landlord is a bit of a dick and has never offered a rolling contract, so each 6 months my workmate signs for another 6 months. His lease is coming to an end at the end of march, by which time it's very unlikely that he will be moved into his new house (offer accepted and mortgage agreed in principle, but the current homeowners haven't found a house to move into yet, so could go on for ages), so he wants to switch to a rolling monthly contract (with one months notice of leaving) when renting so he is in a flexible position to move. His landlord and estate agent are insisting he signs a six month lease, with a fine of £300 if he leaves the contract early, and with my workmate being liable for the remainder of the money owned on the lease if the landlord can't find anyone to live in the property in this duration (i don't see what incentive the landlord has to find anyone in this instance).

so... does he just have to suck up possible paying for maybe 4 or 5 months of renting a
property that he isn't going to be living in?

he could, but that's a massive hassle (i guess he could get all packed up for the new house, move to another rented and just live out of boxes for a while) , and i think it's quite difficult to find somewhere that will initially allow you to be on a rolling month by month contract. I've always had to sign for 6 months initially, tho that's just my experience

has not really pursued this with the landlord to the necessary extent and is just falling back on "he's a prick" because he's lazy or scared of confrontation (not meant to be harsh - loads of people are like this).

If the landlord fully understood the circumstances and that he was def not going to get 6 months out of him there's no logical reason he wouldn't take what he can get out of it without the need for legal recourse. He'd need to be more than a bit of a prick to not realise that.

he automatically goes onto a rolling tenancy anyway. So if they went ahead with the "sign up for six months or you're out" mentality, they still owe him two months' notice.

So he could just refuse the new lease, then it will take the landlord at least 2 months to boot his sorry ass into the gutter as that's the minimum notice period a landlord has to give a tenant. This method is a cost-free means of getting 2 months grace.

The risk is that he could be looking for a new place after 2 months, the possible upside is that his house is ready in the meantime and fuck the landlord.

Pretty sure that if he doesn't sign the new 6 month lease it would take more than a month for it to go down the legal route to get him out, even if he stopped paying rent. If he continues to pay the rent on time then I don't think they have much to pursue on legal grounds - if they tried it most judges would just throw it out as the landlord isn't out of pocket. If he gives as much notice as he can when he gets dates then I shouldn't think they've got any recourse if he hasn't signed.